4-Methyl-3-nitroanisole → 5-Methoxy-o-toluidine

Participants

Reaction Steps

A mixture of 10 gm. (60 mmol) of 3-nitro-4-methylanisole and 4 gm. of 10% Pd/C was stirred under 1 atm. of hydrogen for 30 hours, filtered, and evaporated in vacuo to give 3-amino-4-methylanisole as a residue which was dissolved in 250 ml. of tetrahydrofuran containing 13 gm. (60 mmol) of tert-butyl dicarbonate, refluxed for 3 hours, cooled, and evaporated in vacuo. The residue was chromatographed on silica gel eluting with a gradient 5-10% Et2O /hexane to give 2 (R1=5-OMe), 10.3 gm., 72% yield, mp 72°-74° C.

Provenance & Evidence